EP1885731A1 - Procede de production d'isocyanatosilane et de silylisocyanurate - Google Patents

Procede de production d'isocyanatosilane et de silylisocyanurate

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Publication number
EP1885731A1
EP1885731A1 EP06770968A EP06770968A EP1885731A1 EP 1885731 A1 EP1885731 A1 EP 1885731A1 EP 06770968 A EP06770968 A EP 06770968A EP 06770968 A EP06770968 A EP 06770968A EP 1885731 A1 EP1885731 A1 EP 1885731A1
Authority
EP
European Patent Office
Prior art keywords
cracking
cracking reaction
trimerization
silylorganocarbamate
reaction zone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP06770968A
Other languages
German (de)
English (en)
Other versions
EP1885731B1 (fr
Inventor
Shawn R. Childress
Patrick J. Burns
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Momentive Performance Materials Inc
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Momentive Performance Materials Inc
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Filing date
Publication date
Application filed by Momentive Performance Materials Inc filed Critical Momentive Performance Materials Inc
Publication of EP1885731A1 publication Critical patent/EP1885731A1/fr
Application granted granted Critical
Publication of EP1885731B1 publication Critical patent/EP1885731B1/fr
Active legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888

Definitions

  • This invention relates to processes for making isocyanatosilanes and 1,3,5- tris[(trialkoxysilyl)alkyl]isocyanurates.
  • silylorganocarbamate is vaporized in a reaction zone at elevated temperature, e.g., between 300°C and 600 0 C, to form an isocyanatosilane.
  • U.S. Patent No. 6,008,396 discloses the so-called "hot oil" process for making isocyanatosilanes.
  • a carbamatoorganosilane i.e., a silylorganocarbamate
  • the mixture thus formed is held at a temperature and pressure effective to convert the carbamatoorganosilane to isocyanatosilane.
  • U.S. Patent No. 6,388,117 describes a process of catalytically cleaving (cracking) a carbamatoorganosilane (i.e., a silylorganocarbamate) in the liquid phase to provide isocyanatosilane employing a cleavage and distillation reactor.
  • a portion of the reaction medium e.g., 15-25 weight percent, is purged from the bottom of the reactor in order to keep high molecular weight components at a constant level.
  • the purged material is then allowed to mix with alcohol to quench the isocyanatosilane, is redistilled and a portion thereof is reintroduced to the reactor.
  • DE 10161272 describes a process wherein a silylorganocarbamate is cracked in the presence of a high molecular weight isocyanate and transition metal catalyst.
  • JP 09328489 describes a process where 3-aminopropylsilane is first reacted with isocyanate such as MDI to provide the corresponding urea which is then thermally cracked in the presence of catalyst to provide isocyanatosilane.
  • a number of processes for making isocyanatosilanes utilize low temperature cracking of a carbamate derivative.
  • U.S. Patent No. 4,697,009 describes a process for making isocyanatosilane wherein an acyl-urea group is utilized as the leaving group rather than alkyl alcohols which are most common. This process suffers from the intermediate preparation that involves difficult separation of solvent and the resulting salt.
  • U.S. Patent No. 4,064,151 discloses the preparation of isocyanatosilane by preparing a halosilyl carbamate by direct reaction of aminosilane in the presence of carbon dioxide and halosilyl compounds and a tertiary amine acid scavenger.
  • the resulting halosilyl carbamate decomposes at a relatively low temperature to yield the isocyanatosilane. A difficult workup is required to obtain the product.
  • Typical of non-cracking methods for making isocyanatosilanes are those described in JP 09208589 and U.S. Patent No. 4,654,428 in which an aminopropylsilane is directly reacted with highly toxic phosgene to yield the desired isocyanate.
  • U.S. Patent No. 4,880,927 describes a process for preparing silylisocyanurate in which the silylisocyanate is thermally treated or heated for cyclization to the trimer in the presence of a strongly basic catalyst such as an alkali metal hydroxide or alkoxide.
  • a strongly basic catalyst such as an alkali metal hydroxide or alkoxide.
  • U.S. Patent No. 5,218,133 describes the cracking of silylorganocarbamate in the presence of cracking catalyst under moderate heating and subatmospheric pressure to a non-isolated isocyanatosilane intermediate and by-product alcohol, the isocyanatosilane then undergoing trimerization in the presence of trimerization catalyst in situ to provide silylisocyanurate.
  • Typical cracking catalysts for this process include aluminum, titanium, magnesium and zirconium alkoxides such as aluminum triethoxide which is indicated to be preferred and tin carboxylates such as dibutyltin dilaurate, dibutyltin diacetate and stannous octoate which are indicated to be preferred.
  • Trimerization catalysts employed in the process of U.S. Patent No. 5,218,133 include sodium methoxide and the alkali metal salts of organic acids such as the sodium, potassium, lithium and cesium salts of glacial acetic acid, propionic acid, butyric acid, hexanoic acid, and the like. Both the cracking catalyst and the trimerization catalyst are present throughout the conversion of the silylorganocarbamate to silylisocyanurate in the process of U.S. Patent No. 5,218,133.
  • a process for the production of isocyanatosilane and silylisocyanurate which comprises:
  • Purging step (d) serves several important purposes: (1) it maintains the cracking reaction medium in the cracking reaction zone under steady-state conditions, (2) it removes impurities that might otherwise accumulate in the cracking reaction zone over time and have a detrimental effect on the reaction kinetics and/or rates, (3) it stabilizes the product isocyanatosilane in the presence of detrimental impurities that may distill overhead due to degrading reaction conditions and (4) it provides feedstocks for the production of silylisocyanurate from a common silylorganocarbamate feedstock.
  • the process of the invention can provide a near quantitative yield of isocyanatosilane and silylisocyanurate, both of which are industrially important products, thereby greatly reducing or eliminating the wastes associated with known processes for making these products.
  • Fig. 1 is a process flow diagram illustrating the process of the invention for the concurrent production of isocyanatosilane in a cracking reaction zone and silylisocyanurate in a trimerization reaction zone.
  • R is a divalent hydrocarbon group of from 2 to 11 carbon atoms, and preferably from 3 to 5 carbon atoms; each R 1 independently is an alkyl or halogenated alkyl group of from 1 to 8 carbon atoms, an aryl group of at least 6 carbon atoms or an aralkyl group of at least 7 carbon atoms; R 2 is an alkyl group having 1 to 8 carbon atoms; X is a hydrolyzable alkoxy group; and, a is an integer from 0 to 3, is cracked, optionally, in the presence of cracking catalyst, under cracking reaction conditions to provide isocyanatosilane of the general formula
  • R, R 1 , R 2 and X have the aforestated meanings.
  • silylorganocarbamate from which the foregoing isocyanatosilane is obtained can be prepared in accordance with any known or conventional process, e.g., the processes of U.S. Patent Nos. 5,218,133 and 6,673,954, the entire contents of which are incorporated by reference herein.
  • the silylorganocarbamate can be prepared by reacting an aminosilane, e.g., an aminoalkyltriethoxysilane such as aminopropyl-trimethoxysilane, aminopropyltriethoxysilane, etc., with a dialkylcarbonate, diarylcarbonate or mixture thereof such as dimethylcarbonate, diethylcarbonate, dipropylcarbonate, dibutylcarbonate, diphenylcarbonate, etc., in the presence of a basic catalyst, e.g., an alkali metal alkoxide such as sodium methoxide (sodium methylate) which, following the reaction to produce the silylorganocarbamate, is neutralized with a carboxylic acid such as formic acid, glacial acetic acid, propanoic acid, butanoic acid, etc. to form the corresponding alkali metal carboxylate, i.e., a carboxylate salt which is useful as a catalyst for the cracking
  • silylorganocarbamate When conducting the cracking operation of this invention in the presence of cracking catalyst, it is advantageous to employ a silylorganocarbamate in the process of this invention which is made with an alkali metal alkoxide subsequently neutralized with carboxylic acid since the cracking catalyst for this operation will then already be present in the silylorganocarbamate reactant. Accordingly, it is a particular aspect of this invention to prepare a silylorganocarbamate in this way for utilization in the cracking step of the process herein. Preparing the silylorganocarbamate reactant in the aforesaid manner obviates the need to remove alkali metal carboxylate salt therefrom which is indicated to be preferred in U.S. Patent No. 5,218,133. If desired, salt present in the silylorganocarbamate can be removed therefrom by known methods such as filtration and/or distillation. Removal of a portion of the salt is advantageous in the cracking zone because the salt acts as a strong trimerization
  • silylorganocarbamate reactant which are useful in carrying out the cracking step of the process of this invention are methyl N-3-(trimethoxysilyl)- propylcarbamate, ethyl N-3-(trimethoxysilyl)propylcarbamate, methyl N-3- (triethoxysilyl)propylcarbamate, methyl N-3-(methyldimethoxysilyl)propylcarbamate, methyl N-3-(dimethylmethoxysilyl)propylcarbamate, methyl N-3-(triethoxysilyl) propylcarbamate, ethyl N-3-(triethoxysilyl)propylcarbamate, methyl N-4- (trimethoxysilyl)butylcarbamate, methyl N-3-(triethoxysilyl)butylcarbamate, and the like.
  • a cracking catalyst When a cracking catalyst is employed, it may be any of those heretofore employed for this reaction, e.g., those disclosed in U.S. Patent No. 5,218,133, the entire contents of which are incorporated by reference herein.
  • the cracking catalyst is selected to be a carboxylate salt, in particular, at least one of ammonium carboxylate, alkali metal carboxylate or alkaline earth metal carboxylate.
  • ammonium shall be understood herein to include the ammonium cation, NH 4 + , and the mono-, di-, tri- and tetrahydrocarbyl-substituted variants thereof.
  • carboxylate shall be understood herein to mean the salt of a monocarboxylic acid, dicarboxylic acid or acid anhydride of up to about 20 carbon atoms and advantageously of up to about 12 carbon atoms.
  • ammonium carboxylate salt cracking catalysts herein are ammonium formate, ammonium acetate, ammonium propanoate, ammonium n- butanoate, ammonium n-pentanoate, ammonium 2-methylpropanoate, ammonium 3- methylbutanoate (valerate), ammonium benzoate, tetramethylammonium acetate, tetraethylammonium acetate, tetrabutylammonium acetate, tetramethylammonium 2- ethylhexanoate, tetraethylammonium 2-ethylhexanoate, tetramethylammonium benzoate, tetraethylammonium benzoate, tetrapropylammonium benzoate, tetrabutylammonium benzoate, and the like.
  • alkali metal carboxylates are lithium formate, lithium acetate, lithium propanoate, sodium formate, sodium acetate, sodium propanoate, sodium n- butanoate, sodium n-hexanoate, sodium oleate, sodium laurate, sodium palmitate, disodium malonate, disodium succinate, disodium adipate, and the like.
  • alkaline earth metal carboxylate cracking catalysts herein are the calcium, magnesium and barium carboxylates derived from formic acid, acetic acid, propanoic acid, n-butanoic acid, and the like.
  • the alkali metal carboxylates are readily available or are easily manufactured, e.g., in situ, and generally provide good results.
  • Alkali metal formates are especially advantageous for use herein in that they appear to be more readily removed by filtration from the reaction product mixture than, say, the corresponding acetates and carboxylates of higher carboxylic acids.
  • the alkali metal carboxylate salt is advantageously already present in the silylorganocarbamate reactant due to the manufacturing procedure described above in which the alkali metal alkoxide catalyst used in making the silylorganocarbamate is neutralized post-reaction with carboxylic acid.
  • the alkali metal carboxylate can be generated in situ by the addition of alkali metal alkoxide and carboxylic acid to the silylorganocarbamate and/or previously prepared alkali metal carboxylate can be added to the silylorganocarbamate.
  • the optional carboxylate salt catalyst when utilized herein it will be present in a catalytically effective amount for the cracking reaction. With transfer of a portion of the cracking reaction medium to the trimerization zone, the optional carboxylate salt catalyst will also be present for the trimerization reaction to provide product silylisocyanurate. In general, from about 0.01 to about 1 weight percent, and advantageously from about 0.05 to about 0.2 weight percent, of carboxylate salt catalyst based upon the total amount of silylorganocarbamate in the liquid cracking reaction medium can be utilized with generally good results.
  • the cracking step of the process of the invention can be carried out by heating the silylorganocarbamate-containing reaction mixture, optionally, in the presence of carboxylate salt cracking catalyst, under suitable cracking conditions, e.g., elevated temperature and subatmospheric pressure, for a sufficient period of time for conversion of silylorganocarbamate to isocyanatosilane to take place.
  • suitable cracking conditions e.g., elevated temperature and subatmospheric pressure
  • Gas phase or liquid phase conditions can be utilized. The conditions are advantageously those for liquid phase reaction.
  • cracking reaction medium When the cracking reaction zone is operated under liquid phase conditions, cracking reaction medium will be purged from the cracking reaction zone, i.e., cracking reaction zone 13 of Fig. 1. While an inert organic solvent or mixture of solvents can be employed, ordinarily there is little advantage to doing so. Those skilled in the art can readily optimize the cracking conditions for a particular silylorganocarbamate reactant and, if employed, optional carboxylate salt cracking catalyst, employing straightforward experimental procedures.
  • Residence times ranging from about 1 minute up to about 24 hours, advantageously from about 15 minutes up to about 5 hours, temperatures ranging from about 140°C to about 500°C, advantageously from about 180°C to about 220°C, and pressures ranging from about 5 to about 500 millimeters Hg, advantageously from about 50 to about 300 millimeters Hg, generally provide good results.
  • isocyanatosilane that can be produced in the cracking reaction step are 3- isocyanatopropyltrimethoxysilane, 3 -isocyanatopropylmethyl-dimethoxysilane, 4- isocyanatobutyltrimethoxysilane, 4-isocyanatobutylmethyl-dimethoxysilane, 3- isocyanatopropyltriethoxysilane, 3-isocyanatopropylethyl-diethoxysilane, 3- isocyanatopropyldimethylmethoxysilane, 4-isocyanatobutyltri-ethoxysilane, 3 - isocyanatopropylphenylmethylmethoxysilane, and the like.
  • a predetermined portion of the cracking reaction medium will be continuously or intermittently purged and transferred to the trimerization zone where production of silylisocyanurate takes place.
  • weight percent of the cracking reaction medium based on the weight of incoming silylorganocarbamate feed can be continuously purged from the cracking reaction zone.
  • the purged cracking reaction medium can be transferred directly to the trimerization reaction zone to there undergo conversion to silylisocyanurate or it can be temporarily stored in a holding tank or vessel so that upon completion of the cracking reaction, the stored cracking reaction medium can be reintroduced to the zone from which it was purged, now being operated as the trimerization reaction zone.
  • Conversion of purged cracking reaction medium in the trimerization reaction zone can be represented by the general reaction scheme: purged cracking reaction medium, optionally + R 2 OH containing cracking 7 ⁇ L * "
  • each R, R 1 , X and a have the aforestated meanings.
  • the trimerization reaction can be carried out in the presence or absence of catalyst.
  • catalyst for the trimerization reaction, it will be the same ammonium-, alkali metal- or alkaline earth metal carboxylate catalyst optionally utilized in the cracking operation.
  • Fig. 1 a process flow diagram illustrating the production of isocyanatosilane in a cracking reaction zone operated under liquid phase reaction conditions and concurrent conversion of purged cracking reaction medium to silylisocyanurate in a trimerization reaction zone.
  • Trimerization reaction conditions can be the same as, or different from, those employed in the cracking operation and advantageously include residence times of from about 30 minutes up to about 24 hours, advantageously from about 4 up to about 10 hours, temperatures of from about 150 to about 300°C, advantageously from about 180 to about 220°C, and pressures on the order of from about 5 to about 500 millimeters Hg, advantageously from about 80 to about 300 millimeters Hg.
  • Silylorganocarbamate feed optionally containing ammonium-, alkali metal- and/or alkaline earth metal carboxylate catalyst, in conduit 10 is pre-heated by passage through heat exchanger 11 and introduced via conduit 12 into the base of cracking reaction zone 13 where cracking of the silylorganocarbamate under liquid phase conditions to provide isocyanatosilane and by-product alkanol takes place.
  • the product isocyanatosilane, by-product alkanol and unreacted silylorganocarbamate overheads are introduced through conduit 14 into the base of rectification column 15 which is supplied via conduit 16 with reflux from condensate tank 17.
  • the gas/liquid overheads in rectification column 15 passes via line 18 through condenser 19 to provide technical grade isocyanatosilane condensate containing a small amount of unreacted silylorganocarbamate, e.g., about 5 weight percent or less thereof, which enters condensate tank 17 via line 20.
  • the alkanol overheads in condensate tank 17 passes therefrom via conduit 21 through condenser 22, the alkanol condensate thereafter being transferred via conduit 23 to storage.
  • An isocyanatosilane product in condensate tank 17 is withdrawn therefrom through conduit 24 with a portion thereof being diverted by valve 25 to serve as reflux liquid for rectification column 14 with another portion thereof being transferred through line 26 to storage.
  • the stirred reaction mixture was then rapidly heated to 210°C with initial pressure set at 210 mmHg.
  • the temperature was maintained at about 210°C for 1 hr.
  • the pressure was gradually reduced to 90 mmHg during this period.
  • the mixture was then cooled and filtered.
  • the conversion which was measured by disappearance of the combined carbamate/isocyanate peaks using gas chromatography, was found to be 89 percent.
  • the l,3,5-tris[3- (trimethoxysilyl)propyl]isocyanurate made up approximately 71 wt. percent of the final mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
EP06770968A 2005-06-03 2006-05-23 Procede de production d'isocyanatosilane et de silylisocyanurate Active EP1885731B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/144,464 US7825243B2 (en) 2005-06-03 2005-06-03 Process for the production of isocyanatosilane and silylisocyanurate
PCT/US2006/019943 WO2006132799A1 (fr) 2005-06-03 2006-05-23 Procede de production d'isocyanatosilane et de silylisocyanurate

Publications (2)

Publication Number Publication Date
EP1885731A1 true EP1885731A1 (fr) 2008-02-13
EP1885731B1 EP1885731B1 (fr) 2009-11-11

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Country Status (12)

Country Link
US (1) US7825243B2 (fr)
EP (1) EP1885731B1 (fr)
JP (1) JP5129125B2 (fr)
KR (1) KR20080019267A (fr)
CN (1) CN101189246B (fr)
AT (1) ATE448235T1 (fr)
BR (1) BRPI0610483B1 (fr)
DE (1) DE602006010365D1 (fr)
HK (1) HK1111700A1 (fr)
RU (1) RU2007149550A (fr)
TW (1) TWI376382B (fr)
WO (1) WO2006132799A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3272758A1 (fr) 2016-07-22 2018-01-24 Evonik Degussa GmbH Procede de production de tri [3-(alkoxysilyle) propyl]isocyanurates
EP3372608A1 (fr) 2017-03-08 2018-09-12 Evonik Degussa GmbH Procédé de préparation de tris[3-(alkoxysilyl)propyl]isocyanurates
EP3372609A1 (fr) 2017-03-08 2018-09-12 Evonik Degussa GmbH Procédé de préparation de tris[3-(alkoxysilyl)propyl]isocyanurates
US10377776B2 (en) 2017-03-08 2019-08-13 Evonik Degussa Gmbh Process for preparing tris[3-(alkoxysilyl)propyl]isocyanurates

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US7060849B1 (en) * 2005-09-15 2006-06-13 General Electric Company Method for production of isocyanatosilanes
CN101805366A (zh) * 2010-04-19 2010-08-18 浙江胡涂硅有限公司 三(3-三甲氧基硅基丙基)异氰脲酸酯的制备方法
US8697291B2 (en) 2010-10-07 2014-04-15 Uchicago Argonne, Llc Non-aqueous electrolyte for lithium-ion battery
DE102012219324A1 (de) * 2012-10-23 2014-04-24 Evonik Industries Ag Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren
JP6029926B2 (ja) * 2012-10-23 2016-11-24 浜松ホトニクス株式会社 紫外光発生用ターゲット、電子線励起紫外光源、及び紫外光発生用ターゲットの製造方法
EP3169690B1 (fr) * 2014-07-14 2018-12-05 Momentive Performance Materials Inc. Procédé de production d'isocyanato-organosilanes peu colorés et de couleur stable et produits dérivés de ces derniers
WO2018116941A1 (fr) * 2016-12-22 2018-06-28 パナソニックＩｐマネジメント株式会社 Batterie secondaire à électrolyte non aqueux
US10266554B2 (en) 2017-05-31 2019-04-23 Momentive Performance Materials Inc. Preparation of isocyanatosilanes
CN109503647B (zh) * 2017-09-15 2021-09-21 张家港市国泰华荣化工新材料有限公司 3-异氰酸酯基丙基三甲氧基硅烷的制法
WO2020014040A1 (fr) * 2018-07-13 2020-01-16 Momentive Performance Materials Inc. Préparation d'isocyanatosilanes

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3272758A1 (fr) 2016-07-22 2018-01-24 Evonik Degussa GmbH Procede de production de tri [3-(alkoxysilyle) propyl]isocyanurates
EP3372608A1 (fr) 2017-03-08 2018-09-12 Evonik Degussa GmbH Procédé de préparation de tris[3-(alkoxysilyl)propyl]isocyanurates
EP3372609A1 (fr) 2017-03-08 2018-09-12 Evonik Degussa GmbH Procédé de préparation de tris[3-(alkoxysilyl)propyl]isocyanurates
US10364260B2 (en) 2017-03-08 2019-07-30 Evonik Degussa Gmbh Process for preparing tris[3-(alkoxysilyl)propyl] isocyanurates
US10377776B2 (en) 2017-03-08 2019-08-13 Evonik Degussa Gmbh Process for preparing tris[3-(alkoxysilyl)propyl]isocyanurates
US10703769B2 (en) 2017-03-08 2020-07-07 Evonik Operations Gmbh Process for preparing tris[3-(dialkylalkoxysilyl)propyl]isocyanurates
US10711018B2 (en) 2017-03-08 2020-07-14 Evonik Operations Gmbh Process for preparing tris[3-(alkyldialkoxysilyl)propyl]isocyanurates

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KR20080019267A (ko) 2008-03-03
US7825243B2 (en) 2010-11-02
CN101189246B (zh) 2012-08-08
RU2007149550A (ru) 2009-07-20
BRPI0610483A2 (pt) 2010-06-22
ATE448235T1 (de) 2009-11-15
JP2008542373A (ja) 2008-11-27
EP1885731B1 (fr) 2009-11-11
US20060276644A1 (en) 2006-12-07
HK1111700A1 (en) 2008-08-15
TW200710094A (en) 2007-03-16
BRPI0610483B1 (pt) 2015-08-25
JP5129125B2 (ja) 2013-01-23
CN101189246A (zh) 2008-05-28
DE602006010365D1 (de) 2009-12-24
WO2006132799A1 (fr) 2006-12-14
TWI376382B (en) 2012-11-11

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